Sodium Bicarbonate → HCID 15480996, compound

HRID 1634324Notes

Reaction equation

HRID 1634324 reaction equation
Cl.Cl.[C:3]1([C@H:9]2[C@@H:14]([NH2:15])[CH2:13][CH2:12][CH2:11][NH:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:16]([C:23]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][C:24]=1[CH:25]=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:16]([C:23]1[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:27][C:24]=1[CH2:25][NH:15][C@H:14]1[CH2:13][CH2:12][CH2:11][NH:10][C@H:9]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 15480995HCID 15480995, compoundHCID 69654807(2S,3S)-2-Phenylpiperidin-3-amine dihydrochloride

Product 1

HCID 15480996HCID 15480996, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of Compound 1 (150 mg, 0.60 mmol) and Compound 6 (160 mg, 0.60 mmol) in dry CH2Cl2 (6 ml) was added NaBH(OAc)3 (179 mg, 0.84 mmol) portionwise under nitrogen at room temperature. The reaction mixture was stirred at room temperature for 3 hr. This was basified with sat. NaHCO3 aq., extracted with CH2Cl2, dried with MgSO4, and concentrated to give crude (2S,3S)-3-(2-phenoxy-5-(trifluoromethyl)benzyl)amino2-phenylpiperidine as a yellow oil. This was purified with chromatography to give pure (2S,3S)-3-(2-phenoxy-5-(trifluoromethyl)benzyl)amino-2-phenylpiperidine as a yellow oil (135 mg). This was diluted with ethyl acetate, added HCI-MeOH, and concentrated. The white solid was recrystallized from MeOH-ether to give Compound 7 as a white crystalline (108 mg, 36.0%).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a0c133704f15452e9eca2386aef188d0
Source dataset
uspto-grants-2003_01
Patent number
US06506775B1

Reaction notes

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